Phosphine-free Sonogashira coupling: reactions of aryl halides catalysed by palladium(II) complexes of azetidine-derived polyamines under mild conditions

Tetrahedron

Volumn 65, Issue 8, 2009, Pages 1630-1634

  Lee, Dong Hwan ^a   Lee, Young Hoon ^b   Harrowfield, Jack M ^c   Lee, Ik Mo ^a   Lee, Hong In ^b   Lim, Woo Taik ^d   Kim, Yang ^e   Jin, Myung Jong ^a  

^a Inha University   (South Korea)

^b Kyungpook National University   (South Korea)

^c UNIVERSITÉ LOUIS PASTEUR   (France)

^d Andong National University   (South Korea)

^e Kosin University   (South Korea)

Author keywords

Non phosphine catalysis; Pd complexes; Pyridylazetidines; Sonogashira coupling

Indexed keywords

AZETIDINE; CHLORIDE; HALIDE; PALLADIUM COMPLEX; PHENYLACETYLENE; PHOSPHINE; POLYAMINE DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; CATALYST; PRIORITY JOURNAL; REACTION ANALYSIS; SONOGASHIRA REACTION;

EID: 58249096351     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.12.032     Document Type: Article

References (54)

1. For reviews of metal-catalyzed cross-coupling reactions, see:
2. Diederich F., and Stang P.J. Metal-Catalyzed Cross-Coupling Reactions (1998), Wiley-VCH, New York, NY
3. de Meijere A., and Diederich F. Metal-Catalyzed Cross-Coupling Reactions. 2nd ed. (2004), Wiley-VCH, Weinheim
4. Beller M., and Bolm C. Transition Metals for Organic Synthesis. 2nd ed. (2004), Wiley-VCH, Weinheim
5. Johnson J.B., and Rovis T. Angew. Chem., Int. Ed. 47 (2008) 840
6. For recent reviews:
7. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. 41 (2002) 4176
8. Negishi E., and Anastasia L. Chem. Rev. 103 (2003) 1979
9. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4442
10. Doucet H., and Hierso J.-C. Angew. Chem., Int. Ed. 46 (2007) 834
11. Nájera C., and Chinchilla R. Chem. Rev. 107 (2007) 874
12. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. 44 (1975) 4467
13. McGaffin G., and de Meijere A. Synthesis (1994) 583
14. Chow H.-F., Wan C.-W., Low K.-H., and Yeung Y.-Y. J. Org. Chem. 66 (2001) 1910
15. Novák Z., Szabo A., Répási J., and Kotschy A. J. Org. Chem. 68 (2003) 3327
16. Adjabeng G., Brenstrum T., Frampton C.S., Robertson A.J., Hillhouse J., McNulty J., and Capretta A. J. Org. Chem. 69 (2004) 5082
17. Hierso J.-C., Fihri A., Amardeil R., and Meunier P. Org. Lett. 6 (2004) 3473
18. Bedford R.B. Chem. Commun. (2003) 1787
19. Alonso D.A., Nájera C., and Pacheco M.C. Adv. Synth. Catal. 345 (2003) 1146
20. Consorti C.S., Flores F.R., Rominger F., and Dupont J. Adv. Synth. Catal. 348 (2006) 133
21. Yang F., and Wu Y. Eur. J. Org. Chem. (2007) 3476
22. Hundertmark T., Littke A.F., Buchwald S.L., and Fu G.C. Org. Lett. 2 (2000) 1729
23. Batey R.A., Shen M., and Lough A.J. Org. Lett. 4 (2002) 1411
24. Eckhardt M., and Fu G.C. J. Am. Chem. Soc. 125 (2003) 13642
25. Ma Y., Song C., Jiang W., Wu Q., Wang Y., Liu X., and Andrus M.B. Org. Lett. 5 (2003) 3317
26. Peris E., and Crabtree R.H. Coord. Chem. Rev. 248 (2004) 2239
27. Köllhofer A., Pullmann T., and Plenio H. Angew. Chem., Int. Ed. 42 (2003) 1056
28. Gelman D., and Buchwald S.L. Angew. Chem., Int. Ed. 42 (2003) 5993
29. Anderson K.W., and Buchwald S.L. Angew. Chem., Int. Ed. 44 (2005) 6173
30. an der Heiden M., and Plenio H. Chem. Commun. (2007) 972
31. Gil-Moltó J., and Nájera C. Eur. J. Org. Chem. (2005) 4073
32. Park S.B., and Alper H. Chem. Commun. (2004) 1306
33. Bandini M., Luque R., Budarin V., and Macquarrie D.J. Tetrahedron 61 (2005) 9860
34. Li P.-H., and Wang L. Adv. Synth. Catal. 348 (2006) 681
35. Cai M., Xu Q., and Wang P. J. Mol. Catal., A: Chem. 250 (2006) 199
36. Herrmann W.A. Angew. Chem., Int. Ed. 41 (2002) 1290
37. Herrmann W.A., Öfele K., Preysing D.V., and Schneider S.K. J. Organomet. Chem. 687 (2003) 229
38. Crudden C.M., and Allen D.P. Coord. Chem. Rev. 248 (2004) 2247
39. Dhudshia B., and Thadani A.N. Chem. Commun. (2006) 668
40. Kantchev E.A.B., O'Brien C.J., and Organ M.G. Angew. Chem., Int. Ed. 46 (2007) 2768
41. Alonso D.A., Nájera C., and Pacheco M.C. Org. Lett. 2 (2000) 1823
42. Fairlamb I.J.S., Kapdi A.R., Lee A.F., Sánchez G., López G., Serrano J.J., García L., Pérez J., and Pérez E. Dalton Trans. (2004) 3970
43. Alonso D.A., Botella L., Nájera C., and Pacheco M.C. Synthesis (2004) 1713
44. Alacid E., Alonso D.A., Botella L., Nájera C., and Pacheco M.C. Chem. Rec. 6 (2006) 117
45. Choudary B.M., Madhi S., Chowdari N.S., Kantam M.L., and Sreedhar B. J. Am. Chem. Soc. 124 (2002) 14127
46. Nájera C., Gil-Molto J., Karlstrom S., and Falvello L.R. Org. Lett. 5 (2003) 1451
47. Lee, Y. H.; Harrowfield, J. M.; Kim, Y.; Lim, W. T.; Park, Y. C.; Thuéry, P. Dalton Trans., in press.
48. Lee D.-H., Lee Y.H., Kim D.I., Kim Y., Lim W.T., Harrowfield J.M., Thuéry P., Jin M.-J., Park Y.C., and Lee I.-M. Tetrahedron 64 (2008) 7178
49. Otwinowski Z., and Minor W. Methods Enzymol. 276 (1997) 307
50. Bruker-AXS (ver. 6.12), XPREP, Program for Automatic Space Group Determination (2001), Bruker AXS, Madison, Wisconsin, USA
51. Sheldrick G.M. Acta Crystallogr. A46 (1990) 467
52. Sheldrick G.M. SHELXS97-2 and SHELXL97-2 (1997), University of Göttingen, Göttingen, Germany
53. Stefankiewicz A.R., Walesa M., Jankowski P., Ciesielski A., Patroniak V., Kubicki M., Hnatejko M., Harrowfield J.M., and Lehn J.-M. Eur. J. Inorg. Chem. (2008) 2910 and references therein
54. McKinnon J.J., Jayatilaka D., and Spackman M.A. Chem. Commun. (2007) 3814